3 Leadership Lessons Learned from Selling Software

I’ve spent the last 25 years selling software — first for others, and then as the head of my own company. In that time I’ve learned many lessons that helped me develop my own skills, and then develop the skills of people who worked for me. Here are my top three:

People buy from peopleI learned this lesson early in my career, and then made it a foundation of my software company. People buy from people, not companies; and more importantly, they buy from people they trust. Trust in this context means that your prospects must see you not necessarily as a salesperson, but as a strategic advisor who understands their challenges and knows how to resolve them.

What’s the best way to build this type of trust? In my experience, through face-to-face, in-person meetings. In a world where everyone seems to use texting, emails, and phone calls to build business relationships, the salesperson who makes an effort to meet prospects in person will stand out the most. That’s why I’m constantly pushing my salespeople to meet their prospects face-to face. Our team attends numerous trade shows and industry conferences every year to connect with new prospects and established connections.

The value that face-to-face impressions add to your business cannot be overstated and can be the difference-maker when it comes to establishing trust — and by extension, closing sales.

Your goal is to make people’s lives easierSoftware solutions add value by improving processes, facilitating communication, eliminating issues, and other benefits that are key to organizational excellence. Over time, that became my motivation and drive as a salesperson. For your next prospect meeting, go in with the mindset of “I need to show the prospect that my solution — and I personally — will help them,” not “I need to get the prospect to buy my solution.” Adopting this mindset, that my products would have a positive impact on people’s lives, helped me improve my selling methods and connect prospects with the solutions they needed.

To convince the prospect that your solution will help them, be sure to ask the right questions early on to uncover their specific pain points and challenges. For example, imagine you are delivering a pitch to a retail supply chain director. Rather than a general statement, a great opening line might be, “My solution will help your team improve accuracy and efficiency throughout the supply chain, which I know is a huge priority for you, with your company’s new omnichannel initiative.”

This statement demonstrates understanding of the prospect’s unique situation, and how the solution will help them resolve it. This depth of understanding can only come from asking good, probing questions early on in the sales process — which will reveal the specific pain points that your solution will resolve.

Rejection is as valuable as successI have experienced a variety of wins and losses throughout my career as a software executive, all of which I hold in the same esteem. I believe that in order to break through plateaus – whether creative, performance or motivational – you need to experience obstacles and setbacks. What you do with these seemingly negative moments ultimately determines whether they will lead to future successes. Early in my career, I took the losses personally, which I quickly learned wouldn’t help me learn from it and move forward.

I remember my first lesson with this — it was early in my career, and I lost a sale that I had pumped all my team’s energy into. Rather than taking the loss personally, I sent the prospect a nice note thanking them for their time and wishing them the best in the future. Years later, that very same prospect became one of our best customers, in part because they remembered our professional response to the lost opportunity. Your reaction to a roadblock should always be polite, respectful, and grateful for the opportunity to learn and grow.

The above are three of the most valuable software sales lessons that I continue to practice myself and relay to my sales teams. They are simple, direct ways to convey wisdom, respect, professionalism, and value to your prospects — all of which contribute to your becoming a better salesperson.

As General Manager of Zebra Analytics, Guy Yehiav is responsible for setting the organic and non-organic growth, leadership strategy, and customer success for the Zebra Analytics business unit. Formerly CEO of Profitect, recently acquired by Zebra Technologies, and a 25-year veteran of the supply chain industry, Guy has held senior… View full profile ›